Ammonium Chloride → HCID 23114779, compound

HRID 748739Notes

Reaction equation

HRID 748739 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1.[F:14][C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1>[F:14][C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[CH:17]([OH:18])[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 27340872-Bromo-4-methylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 23114779HCID 23114779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, a tetrahydrofuran solution (1.5 ml, 3 mmol) of isopropylmagnesium chloride was added dropwise to a tetrahydrofuran (2 ml) solution of 2-bromo-4-methylpyridine (334 μl, 3 mmol) under ice cooling and the mixture was stirred at room temperature for 60 minutes. Under ice cooling, 2,5-difluorobenzaldehyde (328 μl, 3 mmol) was added dropwise to the resulting brown solution. The temperature of the reaction mixture was raised gradually to room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. After drying the solvent, the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (456 mg, 65%) was obtained as needle crystals.

Workup

  1. temperatureThe temperature of the reaction mixture was raised gradually to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. customAfter drying the solvent
  4. customthe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (456 mg, 65%)
  6. customwas obtained as needle crystals

Sources & evidence

ORD record
ord-9cbb1266e4034be99c57b0163ee1635d
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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